Benzyl azide → 1-Phenylmethyl-4-(2,4,6-trimethylphenyl)-5-aminotriazole

HRID 10235

反応式

HRID 10235 の反応式
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[CH2:4][C:5]#[N:6].[CH2:13]([N:20]=[N+:21]=[N-:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CC(C)([O-])C.[K+]>O1CCCC1.O>[C:14]1([CH2:13][N:20]2[C:5]([NH2:6])=[C:4]([C:3]3[C:7]([CH3:12])=[CH:8][C:9]([CH3:11])=[CH:10][C:2]=3[CH3:1])[N:22]=[N:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

6

反応物 3

HCID 12152Benzyl azideHCID 5206982,4,6-TrimethylphenylacetonitrileHCID 23665647Potassium tert-butoxide

生成物 1

HCID 154869821-Phenylmethyl-4-(2,4,6-trimethylphenyl)-5-aminotriazole収率 61%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2,4,6-trimethylbenzyl cyanide (1.0 g, 6.3 mmol), benzyl azide (0.92 g, 6.9 mmol) and potassium t-butoxide (0.78 g, 6.9 mmol) in tetrahydrofuran (10 mL) was stirred at ambient temperature for 2.5 days. The resulting suspension was diluted with water and extracted three times with ethyl acetate. The combined organic layers were dried over MgSO4 and filtered. Solvent was removed in vacuo to give a brown oil. Trituration with ether and filtration afforded a yellow solid (1.12 g, 61% yield): NMR (CDCl3,300 MHz):7.60–7.30 (m, 5H), 7.30–7.20 (m, 2H), 5.50 (s, 2H), 3.18 (br s, 2H), 2.30 (s, 3H), 2.10 (s, 6H); CI-MS: 293 (M+H).

後処理

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customSolvent was removed in vacuo
  5. customto give a brown oil
  6. filtrationTrituration with ether and filtration

出典と根拠

ORDレコード
ord-d57d259249774992a4044291bddceda3
出典データセット
uspto-grants-2006_08
特許番号
US07094782B1

関連ノート

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